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Andy Stitzer is a nice guy. He's shy, considerate, polite, lives alone, rides his bicycle to work at Circuit City, has a pristine collection of action figures, is pathologically nervous around women and at 40 years old, is still a virgin. When his co-workers discover this, they make it their mission to get Andy laid. He reluctantly goes along with their plan, but when he meets Trish, a single mother of three, she changes everything.